Currently we have a bunch of 'satellite' systems that all serve the same purpose and don't have active users. It was looking to be a bit tedious (as we are constantly sending out new systems and such) to have to create a separate user in pfSense for our fluid usage of the network. However, as you have mentioned, if the certificate is compromised then anyone could have access to the network (which only allows access to one IP but that is beside the point) and we'd have to replace the certificate on all the systems.
Is there an easier way to create a user/certificate combination without having to go through so many steps every time? On IPCop, for example, you type in the hostname and one or two other things and it created the user and certificate and everything.